Water → HCID 86583893, compound

HRID 637085Notes

Reaction equation

HRID 637085 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[N:19]([CH2:20][CH2:21][CH2:22][C:23](=[O:25])[CH3:24])[C:18]3[CH:26]=[CH:27][CH:28]=[CH:29][C:17]=3[N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.ClCCl.[IH:33].O>C(OCC)C.CO>[IH:33].[O:25]=[C:23]([CH3:24])[CH2:22][CH2:21][CH2:20][N:19]1[C:18]2[CH:26]=[CH:27][CH:28]=[CH:29][C:17]=2[N:16]=[C:15]1[N:11]1[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]1

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 24841Hydrogen iodideHCID 18465101HCID 18465101, compound

Product 1

HCID 86583893HCID 86583893, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Combine 1-(t-butoxycarbonyl)-4-(1-(4-oxopentyl)-1H-benzimidazol-2-yl)[1,4]diazepane, ethylene ketal (0.9 g, 2.0 mmol) and dichloromethane (20 mL). Cool in an ice bath and add hydriodic acid (0.53 mL, 57%, 4.05 mmol). Warm to ambient temperature. After 0.5 hours, add water (0.5 mL) and heat to reflux. After 18 hours, cool to ambient temperature and evaporate in vacuo to give a residue. Combine the residue and methanol (45 mL) and add diethyl ether (250 mL) with stirring to give a solid. After 30 minutes, collect the solid by filtration to give, after drying the title compound. Elemental Analysis calculated for C17H24N4O.2 HI: C 36.71; H 4.71; N 10.07; Found: C 36.94; H 4.47; N 9.84.

Workup

  1. temperatureCool in an ice bath
  2. temperatureheat to reflux
  3. waitAfter 18 hours
  4. temperaturecool to ambient temperature
  5. customevaporate in vacuo
  6. customto give a residue
  7. customto give a solid
  8. waitAfter 30 minutes
  9. customcollect the solid
  10. filtrationby filtration
  11. customto give
  12. dry with materialafter drying the title compound

Sources & evidence

ORD record
ord-c97e6cfa10054f45a0d91eca2b22e1f9
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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